So, I had a lot of fun troubleshooting this one. The user has a new HP ProBook laptop running Windows 7 and Office 2007. The symptom is that they can not consistently send an email with more than one addressee. When the user sends an email with more than one address, as soon as they hit Send, they receive the error “The operation failed.” This symptom persists on both email accounts associated with the Outlook profile. (A POP3 and an Exchange account)

Searching on this error, I found many variations to its cause, and a lot of proposed solutions. What worked for me, was uninstalling the entire HP ProtectTools suite, and then performing a Repair operation on Office from Add/Remove Programs. I think that approach might be a bit heavy handed, but I was short on time at the moment, and the suite was only interfering with the user’s work, not augmenting it.

If I have the opportunity to work on this again, I’m going to start with HP’s Privacy Manager that hooks into Outlook and installs a toolbar.  Many of the posts I read seemed to have the common theme of killing a third party application that was trying to augment Outlook. If you have this problem, and come across a more elegant solution than nuking HP ProtectTools from orbit, let me know!